Seven Sins
by Mimoliin
Summary: Slight AU (pre-Emma), modern-day Storybrooke tale about a crazy bet between three best friends. Rated M for adult themes, language and smut.
1. The Bet

_Had a hard time falling asleep last night (overactive brain much) and suddenly, this story idea just came to me, like out of nowhere. Decided to write and publish the first chapter before forgetting about it._

_Don't worry though, I'll continue to update _The Missing Princess_ once every other day like I normally do; chapter 12 is as good as finished and will get published tomorrow evening (GMT +1). :-)_

_Hope you'll enjoy this slight AU (pre-Emma = no memories of their lives in the Enchanted Forest), modern-day Storybrooke tale about a crazy bet between three best friends. Short first chapter as it felt natural to break where I did. Following chapters will be longer. _

_Rated M for adult themes, language and smut._

___Disclaimer: I do not own any of the characters presented in this story aside from my OC Cassandra. Everything else belongs to ABC, the creators, producers and distributors of Once Upon a Time._

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**Chapter 1: The Bet**

The lightening inside the local pub was dim and it smelled heavily of cigarette smoke. They'd all three had a couple of drinks each, and were now discussing subjects they normally did not speak that openly about.

"Are you being serious? A year-long draught?" Mary Margaret was looking at the young woman with the long, blonde hair on her opposite side of the table.

"I'm not sure I could handle that myself; I'd literally jump the first available guy after only a couple of weeks. Months tops, but only thanks to my Rabbit." Ruby added to Mary Margaret's sentence.

"Correction Ruby; you'd jump the first guy, available or not." Mary Margaret added. Ruby glared at her friend.

"Well, I'm nothing like you obviously, Ruby. I can't have any of what you would call 'casual sex', there has to be emotions involved for me to even consider giving allowance to my body to any guy. I call it 'making love', ever heard of that yourself?" Cassandra giggled along with her two best friends, both sitting next to her around the tall, black bar-table.

"Sure you can do casual, you just have to open yourself up a little bit more, allow your mind to wander freely. Look at that guy, for example."

Ruby pointed towards a handsome guy, about average height with brown hair, standing by the bar. "Now, force youself to think naughty thoughts about him. Can you feel it?"

"Really, Ruby." Cassandra sighed.

"Yes really, Cass. You need to at least try. Don't do it for us, but for your own sake; a little fun would do you more than good. Imagine him naked." Mary Margaret filled in.

"Look at those large hands of his, we all know what large hands means, don't we?" Ruby exclaimed a little too loud, while having the largest of grins on her lips.

_Think naughty thoughts, Cass. Imagine him naked... Come on, you can do it. Feel it,_ Cassandra thought to herself while trying her best to evoke any feelings of sexual nature dormant somewhere deep inside of her.

"I'm sorry, I can't feel anything." The blonde mumbled disappointedly.

"Are you out of your mind, woman? That guy is totally hot, and you feel nothing while imagining him fully nude? You need help." Ruby had a facial expression as if someone had just offended her.

"Even I would allow him to seduce me. Not saying I'm a saint or anything, but compared to Ruby..." Mary Margaret stated in a cheerful mood.

"Oh, shut up you!" Ruby playfully shoved on Mary Margaret's arm before once again turning to Cass. "Someone once told me; the more sex you have, the more -"

Ruby interrupted herself. "Don't look, but I think mister Naked is on his way over to our table." She whispered as the guy suddenly began to approach the women.

"Seems like you're enjoying yourselves, ladies. I'm Jefferson." Studying all three of them carefully, his eyes finally found their rest on Cassandra. "Can I buy you a drink?"

"Uhm, sure, I guess." Cass responded.

Jefferson instantly returned to the bar.

"You look like a lost little confused puppy with those big, brown, surprised eyes of yours, Cass." Ruby said, eyebrows raised.

"Is it so hard for you to believe someone may actually take interest in you?" Mary Margaret asked Cass. "You're a young, attractive and successful woman after all. And those heels really do magic for your legs."

"Whatever, really. I'm not interested anyway." Cass responded, somewhat annoyed by her friends.

She quickly finished her glass of white wine to make more room on the table, as Jefferson was once again moving towards the women; this time with three orange-colored drinks and one beer in his hands.

"Three sweet drinks for three sweet ladies." He smirked as he put the glasses down before leaving them alone again, returning to his buddy by the bar desk.

"Such a gentleman... If you're not going to hump him, I will." Ruby laughed out loud.

"You know what, perhaps I will, if only to shut the two of you up."

"Now we're talking, Cassandra!" Mary Margaret exclaimed.

"I still don't think you've got it in you, blondie. Prove me wrong and I'll prove you wrong; for every new guy you get intimate with, I'll stay away from all kinds of sexual activity for a month."

Tipsier than she'd been in a long time, and without considering the consequences of her words the slightest, Cass responded. "Make that one year if I manage seven guys in seven days, Ruby."

"I believe we've got ourselves a deal, hun." Ruby was a bit surprised by Cassandra's words, but didn't think she'd ever put them into action.

Cass on the other hand felt motivated and up to the challenge, as she immediately rose from the table.

"If you fail, those heels are mine." Mary Margaret said, lousily faking an evil grin.

"Have fun 'making love', Cass dear." Both women giggled behind her as she left them to approach Jefferson with friend.

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	2. Just One Bite

_Totally in love with this far less complicated (compared to my other) fic already, why I'm updating sooner than originally intended._

_Time to sin, ey!_

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**Chapter 2: Just One Bite**

She was now stood between the two men; Jefferson and a guy who introduced himself as Graham.

_What. The. Fuck. Were. You. Thinking,_ Cassandra thought to herself as Jefferson, now also known as mister Naked, put his arms around her shoulder. _I totally hate Ruby and her extremely stupid bet right now._

Her friends had been right about one thing though; Jefferson did indeed look good. And he smelled like a god too; a combination of masculinity and some kind of expensive, European fragrance. Perhaps it was the alcohol clouding her mind, but she could definitely feel some sort of attraction towards the man. Not the 'I need you right here, right now' kind of attraction Ruby had been badgering about for years, but more of a 'I could learn to like the situation' sort of feeling.

As Graham left to converse with acquaintances of his, Jefferson advanced one step closer to Cass.

"Me and my buds come here occasionally to play pool and have a beer or five. You come here often? I don't think I've seen you before, would've noticed that pretty face anywhere."

Jefferson kept on talking to her, but Cass couldn't concentrate on his words even the slightest as the gaze of her two friends distracted her severely. They were a little bit too curious to find out whether or not Cass would go through with their bet, and they'd both had one drink too many to actually behave.

Staring at his lips move, Cass leaned in to press her mouth against them while making sure Ruby and Mary Margaret were watching. She could distinguish the sounds of two shocked girls not far from herself, gasping at her deliberate and straightforward move.

"Ehh... I don't see how that action answers the question I just asked." Jefferson was looking more than confused, eyebrows raised, while staring at the big, brown eyes in-front of him.

Cassandra turned red out of embarrasment and immediately started to regret her impulsive, uncharacteristic behavior. She'd hoped Jefferson would've had reacted somewhat differently towards her sudden move. For the first time in her life, she actually wished for a guy to be a total creep that wanted nothing but to bang anything with two legs. Jefferson was not that guy, apparently.

"Shit, I am so terribly sorry, I didn't mean to offend your or freak you out or anything, it's just - "

Unsure if telling him about the bet would be her smartest available move - maybe he'd play along, maybe he wouldn't-she decided to keep quiet to avoid startling him any further. He was, after all, guy number one in hers and her friends' evil mastermind plan. She wasn't ready to lose the bet after only a couple of minutes.

"It's just what?"

"Never mind. I haven't been dating, or even flirting for that matter, for more than a year... Guess I'm a bit rusty, that's all."

Her words seemed to have had the intended effect; he looked at her with apologetic eyes, like he was the one being sorry for kissing her and not the other way around. She let out a quiet sigh of relief as the tense atmosphere instantly dissolved.

"Let me help you rid yourself of the rust then, Cassandra, was it?" He smirked at her, showing off his annoyingly perfect teeth, before returning the kiss from before, now with passion.

Lips were locked and tongues were dancing for a moment that felt like an eternity as Cass pulled away from Jefferson to throw a quick glance at her friends. Shocked, surprised and speechless were three words describing their reaction pretty well. If Cassandra's facial expression could speak, it would've told them something similar to; L_ook who's laughing now, bitches._

Their mouths reunited as Jefferson placed his hands on her neck and pulled her closer. She could feel _something_ inside of her as she trailed his muscular arms with her manicured fingernails.

"You want to go somewhere more private, beautiful? I've got a _very_ big and soft bed just waiting for us to keep it warm back at my place." He whispered sensually in her ear.

_Bingo!_

This was the moment of truth. To do or not to do; to win or lose; to fail or succeed. She had to make up her mind, and that fast. Did she really want this man to be the one to take her casual sex-virginity, and was tonight really the night for it?

_Hell-to-the-yes, now is as good a time as any._

"Lead the way, Jefferson." Cass felt like a very bad girl as the sentence escaped her mouth, and to her surprise, she actually liked it.

Cassandra gave Ruby and Mary Margaret her largest grin possible as she and Jefferson walked by their table on their way out of the pub. Ruby managed to unnoticed sneak down a condom, size 'extra large', into the black leather purse that was resting over Cassandra's right shoulder.

"Let's at least _hope_ it'll be a fit". The girls giggled.

"I still believe those heels will become mine one day, Cass." Mary Margaret tauntingly exclaimed behind Cassandra and Jefferson as they left through the doors, holding each other's hands.

* * *

They reached a huge house after a shorter ride in a cab. Cassandra gasped as she realized this was where Jefferson actually lived, and also where she'd spend her night if everything went according to her plans.

"Are you some kind of a billionaire or what?" She asked suspiciously as they entered the building.

"I can be anything you want me to, dear." He smirked playfully.

He closed in on her from behind. Removing the blond hair covering her shoulder, he started to softly kiss her neck. She froze, still unused to his - or anyone's - touch. Hugging her tighter, heavily breathing in her scent, she could feel him pressing hard against her butt.

She panicked and wanted an out. She once again considered telling Jefferson about the bet; it would most definitely make him back off long enough for her to be able to escape his mansion. He could tell she was tense.

"Relax, beautiful. All I want is for you to feel good, but I can't do that if you won't allow me." His fingers found the zipper of Cassandra's little, white dress as he was speaking, slowly pulling it down. "So innocent and pure, just like your dress. Are you sure you want me to continue?" His hand was stroking her just below her breasts, while he kept on trailing wet kisses on her neck and shoulder.

_What's the matter with you? He's without a doubt the hottest guy you've ever been this close to physically, and you want an out? Nope, not going to happen, Cassandra. Relax. Let him touch you. Enjoy it._

Cass decided to somehow let her guard down. She was, after all, curious what it would feel like to let this painfully sexy guy have his ways with her.

"Please, do continue."

Jefferson moved his hand upwards and cupped her left breast with it. It fit perfectly in his palm. He massaged it carefully, while slowly pulling her dress down with his other hand. The dress dropped to the floor once it had gotten past her curvy hips. The sight of Cassandra in nothing but white, lacy underwear made him sigh approvingly.

"You are one beautiful woman." He said as he lifted and carried her up the large stairs that lead to the master bedroom. He didn't put her down until they'd reached that very soft, king size bed of his. The silky, blue sheets were cool against her skin as she was lying there, watching Jefferson undress eagerly. He was undoubtedly taking good care of his body, as his muscles were defined and his skin sun-kissed.

She had felt nothing while imagining him naked, but as the pictures began to materialize in front of her eyes, she could definitely feel something deep inside her core; desire. What was once dormant had started to awake. Cassandra was now sure she wanted him; she wanted his large, hard member to penetrate her.

Completely naked and absolutely gorgeous, he continued giving attention to her breasts. The sheer fabric of her lingerie couldn't conceal her arosed nipples as he circulated them with his thumbs. Her breathing started to intensify, but she made sure to suffocate any moans or cries wanting to escape her throat. She was feeling shy, which she rarely ever did outside of the bedroom.

Jefferson motioned her to sit up. She did, and he unhooked her bra with one quick and skilled movement. His certainty made her feel a little uncomfortable.

_Does he do this a lot? Perhaps you're only miss Saturday to him, just the toy of the night._

Cassandra tried to mentally shake those thoughts off and away. After all, Jefferson was nothing but mister Saturday to herself if she'd go through with the rest of the bet in its full. She was either way worse than him, as she was actually planning her future conquerings, referring to them as simple numbers. Number one, Jefferson, was currently entertaining her nipples with his tongue, while his hands were moving further south with each second passing.

Having reached their current goal, he removed Cass's panties. His fingers started to explore her folds, and she was starting to get wet. The moist made it easy for him to carefully insert the tip of his middle finger. His mouth left her breasts and instead joined his hand between her thighs. Sliding deeper and deeper, his finger was soon entirely inside of her while his tongue brushed and tickled her clit. Cassandra's breathing was heavy, her body shivered, and barely audible little cries made Jefferson confident she was enjoying what he was doing to her body.

Having a hard time keeping her eyes open longer than seconds at a time, Cassandra buried her hands in his brown hair and pressed his head closer to her, motioning him to intensify his touch. He entered her with a second finger and accelerated the movements of his tongue.

Holding her breath out of pure pleasure, her world turned completely black for a short moment, and then it washed over her; an explosion of colors in an orgasm powerful enough to make Cassandra moan out loud.

When she was no longer shaking from the aftershocks of the climax, Jefferson moved up and kissed her passionately, forcing her to taste herself in the process. She felt embarrased and turned on at the same time.

He placed himself by her entrance, and entered with one hard thrust of his hips. _Holy fuck_. Having all of him inside of her hurt her as she hadn't had sex for over a year, but he was also the largest she'd ever been with. She cried a little out of pain before her body adjusted to his now more careful thrusts. It started to feel good; insanely good.

_How could you allow yourself to miss out on this for such a long time, Cass?_

She started to meet his hips with her own movements as they together began moving faster, his cock filling her up completely each time it hit her deepest spot. She felt another wave approaching, and just as her body once again gave in to the amazing touch and feel of the gorgeous man on top of her, he emptied himself with a loud moan.

To with a stranger experience the most intimate thing possible was something she'd never thought she'd ever do previous to that night. The bet didn't feel quite as impossible to her anymore. Ruby would probably get a rough year, though.

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	3. The Hangover

_Currently spending almost every free minute on 'The Missing Princess' (go check out 'Chapter 14: A Perfect Storm' which I uploaded today! :-) ), why I'll be updating this story approximately once a week. Perhaps more often, but not less._

_So, how does Cassandra feel after her escapades with Jefferson? And who will be mr. Sunday?_

_Let's find out, shall we?_

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**Chapter 3: The Hangover**

Walk of shame. The ultimate humiliation.

Wearing yesterday's dress and make-up, along with tousled hair and a feeling of guilt inside of her stomach, wasn't something she enjoyed even the slightest; but to do so in bright daylight with the curious eyes of the townsfolk watching her as she progressed on the sidewalk with her heels in her hands was nothing but mortifying.

_They know. They so know I'm on my way home after having had a bit too much of fun last night._

She'd finally reached her building. She unlocked the door, entered her apartment and threw her keys on the coffee table next to the couch where she crashed, embarrassed and ashamed of herself. What had felt like a brilliant idea last night, now made her feel both dirty and vulnerable.

She fumbled with her iPhone. _Perhaps calling Jefferson would make me experience less discomfort,_ she thought before realizing she didn't receive his phone number. _Crap._

She opened and scrolled through her contacts. "Yeah, what the heck." She murmured as she called Ruby.

"If it isn't miss Brave!" Ruby sounded cheerful as ever.

"Yeah, go ahead and make me feel even worse. I did a terrible, terrible mistake last night. Remind me I'm staying sober from this day onward." Cassandra sighed.

"You sound like a nun or something, Cass. This is the 21st century darling, no one should feel ashamed of having sex, especially not protected such! I just assume you're _that_ smart." Ruby exclaimed.

"You wern't as discrete as you think you were, planting that condom in my purse. Thanks, though. It was a perfect fit."

They both giggled before Cass continued, now serious again.

"My logic knows you're right, but I feel totally awkward. I even left my panties at Jefferson's place as I wanted to get out of there as quickly as possible. I want to draw a bath and just sleep off the hangover in my tub until all the filth has vanished from my body." She stroke her arm with the tip of her fingers as she uttered the last sentence, as if she was actually trying to feel the non-existent impurities on her skin.

"Hey, Cassandra, knock it off. I would understand how you feel if the guy you were with wasn't a complete hottie. You should really be celebrating instead of complaining. I'm gonna hang up on you now, call me back once you have something positive to say, okay?"

Cassandra buried her face in a purple silk pillow.

* * *

She awoke to a loud, banging sound. She had fallen asleep on the couch, with her phone still in her hand. _Fuck, what time is it?_

"Cass, you in there?" Mary Margaret yelled from the opposite side of the door.

Large numbers on her display stared back at Cassandra. Seven thirty.

She had not forgotten about her plans with Mary Margaret, but she had not planned on falling asleep as early as noon that Sunday. Well, she hadn't planned staying the previous night at someone else's either.

"Just give me a second, I'll be right out with you!" Cass shouted back as she escaped her little white dress and grabbed a sheer, powdery-beige blouse and a pair of blue jeans.

_Still no panties, and no bath. You're such a mess Cass, shape up!_

She combed through her blonde hair by the large mirror in the hallway, while simultaneously trying her best to get dressed. She removed some dried mascara off the delicate skin underneath of her dark-brown eyes and added a neutral gloss to her lips.

_That'll do, it's only a casual dinner with Mary Margaret anyways._

To her surprise, Mary Margaret wasn't alone. She'd brought along three friends she'd met at a charity event earlier that week.

"I thought it would be just the two of us." Cass whispered in Mary Margaret's ear.

"Yeah, well, plans changed and I tried to inform you, but you didn't answer when I called. I thought maybe something had happened to you, you almost had me worried for a second. That's why I decided to come by here in the first place, even though we'd agreed upon meeting at the restaurant."

Cassandra mumbled something barely audible to Mary Margaret before she turned towards the new faces. She shook hands with the woman, Belle, first; a gorgeous girl about the same age as Cassandra, perhaps a little older. Cass then introduced herself to the two guys; Robin, probably thirty plus with a masculine stubble on his chin, and Phillip, a few years younger than Robin, with brown hair and amber eyes.

They walked the few blocks to the restaurant - a small but cozy place with red interior and dark wooden furnishing. The company sat down and ordered in two bottles of wine, one red and one white, that would go well with the place's meaty menu. As the waitor, pouring the wine into large, rounded glasses, approached Cassandra, she politely asked for a diet coke instead of the alcoholic beverages the rest of the company would enjoy throughout the evening. Yesterday's all-out, crazy partying had been more than enough to her.

Robin, who was sitting on Cassandra's opposite side at the rectangular table, ordered in a beer in addition to the red wine he'd just been served. It seemed to Cassandra that he and Phillip might have had a few beers before they'd met up with Mary Margaret earlier that night. They were loud and gesticulatory as they were bantering and telling jokes the whole restaurant could hear. Once every now and then, Robin addressed Cass specifically, and it made her remember...

_Shit. The bet. _

She knew she would have to seduce one of the guys at the table to not lose the bet. A thought about lying to her friends, Ruby and Mary Margaret, crossed her mind. She could tell them she did indeed hook up with a guy that night, if it wasn't for the fact that Mary Margaret was going to spend the entire evening in company of her. Mary Margaret would know if Cass lied.

As their food arrived and they picked up their cutlery, she threw a quick glance at the men's hands.

_No rings on their fingers, that's good. Belle seems somewhat into Phillip though, I don't want to ruin anything that might be going on there. Robin it is then, I guess._

Cassandra felt awkward again. A glass of wine could really help her get into the mood, but it would also make her feel worse tomorrow. She sighed loudly, uncertain what to do next.

"Sup sweetie?" Robin had noticed that Cassandra was deep in thought.

"Nothing, I was just thinking about... work related stuff." She put on her most convincing fake smile, showing off her artificially whitened teeth. She'd, however, gotten Robin's full attention by now.

She quickly sent Mary Margaret a text underneath the table: "Robin single?"

Mary Margaret grinned at Cassandra before replying: "Hahaha! He is indeed. Go for it, devil!"

_Well... here we go, then!_

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**If you've read it, please leave a review with your thoughts, questions, suggestions etc; please let me know if you like or dislike the story! :-)**


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